Journal of Advances in Medical and Pharmaceutical Sciences 5(1): 1-10, 2016, Article no.JAMPS.21743 ISSN: 2394-1111

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Review of Phytochemical, Pharmacological and Toxicological Profile of kunthianum

J. J. Oloche 1* , F. Okwuasaba 2 and G. O. Obochi 3

1Department of Pharmacology, College of Health Sciences, Benue State University, Makurdi, Benue State, Nigeria. 2Department of Pharmacology, Faculty of Pharmaceutical Sciences, University of Jos, Plateau State, Nigeria. 3Department of Biochemistry, College of Health Sciences, Benue State University, Makurdi, Benue State, Nigeria.

Authors’ contributions

This work was carried out in collaboration between all authors. Author JJO designed the study and wrote the first draft of the manuscript. Author FO reviewed the study design and presentation of the work. Authors JJO and GOO managed the literature searches. All authors read and approved the final manuscript.

Article Information

DOI: 10.9734/JAMPS/2016/21743 Editor(s): (1) Palmiro Poltronieri, National Research Council of Italy, CNR-ISPA, Italy and Institute of Sciences of Food Productions, Operative Unit in Lecce, Italy. Reviewers: (1) Anonymous, University of Sao Paulo, Brazil. (2) Guo-Qing Zhong, Southwest University of Science and Technology, Mianyang, China. (3) Anonymous, Quaid-i-Azam University, Islamabad, Pakistan. Complete Peer review History: http://sciencedomain.org/review-history/11698

Received 1st September 2015 nd Review Article Accepted 22 September 2015 Published 6th October 2015

ABSTRACT

Aims: The review is directed at the phytochemical, pharmacological and toxicological activities of the medicinal Stereospermum kunthianum, Cham, () widely distributed in the Guinean-savannah. Results: A survey of previous scientific publications and available literatures revealed that tannins, saponins, flavonoids, terpenoids, glycosides, sterols, coumarins, quinones and higher fatty acids have been isolated with various solvents from different parts of the plant. Extracts from the plant have shown antibacterial, antiplasmodial, , anti-inflammatory, antidiarrhoeal, anticonvulsant and antioxidant activities pharmacologically. Sub-acute and acute toxicity studies

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*Corresponding author: E-mail: [email protected];

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showed that Stereospermum kunthianum has a wide safety margin up to 1000 mg/kg b. wt. and can be used for long term treatment of disease conditions for which it is indicated. Conclusion: Result emerging from the review of scientific studies unveil the therapeutic potential of Stereospermum kunthianum extracts and isolated compounds thereby justifying the use of the plant in traditional medicine as a remedy for treatment of various diseases in humans.

Keywords: Medicinal ; extracts; activity; isolated.

1. INTRODUCTION caniculate. Immature leaves are occasionally toothed and hairy [6]. The use of medicinal plants is as old as human civilization [1]. Medicinal preparations derived The pods are chewed with salt to treat coughs from plants have been in widespread use and and are used in treatment of ulcers, leprosy, skin considered in ancient times as a connection to eruptions and venereal diseases, while the stem the divine [2,3]. Medicinal plants have been used bark decoction or infusion is used to cure as a means of curing or preventing diseases and bronchitis, pneumonia, cough, rheumatic arthritis traditional medicine is still the first point of and dysentery [7]. The roots and leaves have healthcare for many people in sub-Saharan been found useful in treating venereal diseases, Africa where there has been a long and rich respiratory ailments, gastritis [7]. Analgesic and tradition of obtaining treatments from herbs and anti-inflammatory activities of stem bark [8], as trees [3,4]. Although incorporating traditional well as the anthelmintic activity of ethanol leave medicine into the national health system is not a extract has been reported [9]. Other priority in Nigeria, WHO recognizes traditional pharmacologic activities such as, antibacterial, medicine as a vital health-care resource [5]. antidiarrhoeal and antiplasmodial activity of lipophilic root bark extract have also been Scientifically proven therapeutically active reported [10-12]. Parts of the plant often used for substances are present in different medicinal ethnomedicinal purpose are leaves, stem bark plants, one of which is Stereospermum and root bark. kunthianum (S. kunthianum) . S. kunthianum (Cham, Sandrine Petit), family Bignoniaceae, Numerous scientific studies which unveil the synonyms; Stereospermum dentatum A. Rich, therapeutic potentials of the plant extract or Bignonia lanata R.Br, Dolichandrone smithii , isolated active phytochemical compounds such Stereospermum arguezona A. Rich, as tannins, saponins, flavonoids, glycosides, Stereospermum cinereoviride K. Schum, sterols, terpenoids, cooumarins, Stereospermum integrifolium A. Rich [6]. naphthaquinones and anthraquinones which account for the medicinal value of the plant have S. kunthianum is a small woody tree of about 5 been elucidated. But the isolation and or 15 m high and diameter 25 cm. It is found in characterization of phytochemical constituents the Sudano-Guinea savannah regions of Africa and the mechanisms by which it exerts some of and Asia, where the plant parts are used to treat its pharmacological and toxicological activity various ailments [7]. It has thin, grey-black bark, have only been partly investigated. Thus, this smooth or flaking in patches, the trunk is rarely study is a thorough review of phytochemical, straight, with twisted branches with abundant, pharmacological and toxicological studies of fragrant, precocious, pink or purplish flowers, S. kunthianum aimed at providing information making the tree a spectacular sight. The available in scientific literatures thereby revealing alternate leaves are imparipinnately compound opportunities for further research work required and some 25 cm long; leaflets are nearly for complete assessment of the therapeutic opposite with one terminal leaflet, and with short, benefits of the plant. soft hairs, oblong to oblong-elliptic in shape, green and hairless above, yellowish-green with 2. PHYTOCHEMICALS OF S. kunthianum prominent venation below, apex somewhat attenuate, and the base tapering. The leaf Phytochemical analysis of the plant extracts of margin may be entire or sometimes toothed in S. kunthianum was done using standard tests; coppice shoots, while petiolules are virtually Wagner test for alkaloids, foam test for saponins, absent. Petioles may be up to 7 cm long, and are ferric chloride, gelatin and lead acetate tests for

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the presence of phenolic compounds and and leave extracts of S. kunthianum by MS, UV flavonoids. Data from phytochemical studies of and NMR spectra are compound 4; quercitin, 5; extracts of S. kunthianum verifies the presence luteolin, 6; rutin, 7; 3,7,4̍-trihydroxy-3-̍ (8̍̍-acetoxy- of tannins, saponins, flavoniods, terpenoids, 7̎̍-methyloctyl)-5,6-dimethoxyflavone, 8; polyphenols, higher fatty acids, coumarins, isoquercetin and 9; kaemferol (Fig. 2) sterols, naphthaquinones, anthraquinone and [18,14,12,19]. An example of flavonoid isolated glycosides in the plant [10,11,13-15]. Three from S. kunthianum with antidarrhoeal activity is phytochemicals of utmost interest in this species dimethoxyflavone [12]. are glycosides, flavonoids and quinones. 2.3 Sterols of S. kunthianum 2.1 Glycosides of S. kunthianum In a review [20] reported that compound 10 ( β- There is a wide distribution of iridoid ester sitosterol) shown in Fig. 3 and β-sitosterol glycosides and recognized as one of the glucoside exhibited good pharmacologic activity important markers in plants belonging to in hypercholesteremia, wound healing, Bignoniaceae family [16]. These glycosides have inflammation, helminthiasis, management of been associated with antimicrobial activity pain, diabetes, as an antioxidant and in certain thereby justifying its use as antiseptic in types of cancers. Petroleum ether extract of S. traditional medicine [17]. Iridoid glycosides kunthianum containing sterols subjected to thin isolated from the stem bark extracts of layer chromatography, using normal phase silica the plant were 6-O-trans-p-coumaroyl- gel as stationary phase and petroleum ether: decinnamoylglobularimin (stereospermiside ; 1), chloroform, hexane: ethyl acetate or chloroform: (3,4-dihydroxyphenyl)-ethyl-O-α- methanol as mobile phase, the chromatograms rhamnopyranosyl-3,4̍ ̍-dihydroxycinnamoyl-β-D show identical zones for steroidal nucleus with glucopyranoside (stereospermin; 2), 1,6-di-O- reagents. Structural elucidation carried out by cinnamoyl-β-glucopyranoside {stereostin; 3} [13] various spectral data from 1H- and 13C-NMR, IR and phenylpropanoid glycosides. The chemical and Mass spectroscopy confirmed the presence structures are shown in Fig. 1. of two phytosterols; β-sitosterol and β-sitosterol glucoside [13]. 2.2 Flavonoids of S. kunthianum

Flavonoids are partly responsible for the anti- 2.4 Quinones of S. kunthianum diarrheal activity of S. kunthianum [17,12]. The preliminary phytochemical screening of the Five naphthoquinones; pinnatal, sterekunthals A, petroleum extracts revealed that the sterekunthal B, pyrankunthone A, antidysenteric and antidiarrheal properties of pyrankunthone B and one anthraquinone; medicinal plants were due to tannins, alkaloids, anthrakunthone were isolated from lipophilic root saponins, flavonoids, steroids, terpenoids and bark extract of S. kunthianum (Table 1) were reducing sugars [11,15]. Flavonoids that have reported to exhibit antiplasmodial activity [10]. been isolated and characterized from stem bark

1 2 3

Fig. 1. Chemical structures of S. kunthianum glycosides

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4 5 6

7 8 9

Fig. 2. Chemical structures of flavonoids of S. kunthianum

10

Fig. 3. Chemical structure of sterol S. kunthianum

Table 1. Phytochemical profile of S. kunthianum

Plant part Type of extract Phytochemical Reference Root bark Petroleum ether Naphthoquinone (sterekunthals A, [10,17,22 ] sterekunthal B, pyrankunthones A, pyrankunthones B, pinnatal) Anthraquinone (anthrakunthone) Stem bark, Methanol extract Glycoside (stereospermiside, [13,22,18,21 ] leave stereospermin and stereostin) Glycosides of ferulic acid Stem bark, Aqueous-acetone Flavonoids (rutin, isoquercitin, [22,18,14,21 ] leave quercitin and luteolin) Kaepferol Dimethoxyflavone Aqueous-acetone Coumarin (sinapic p- coumaric acid) [11,18,21 ] Leave Petroleum ether, Phytosterol ( β-sitosterol, β-sitosterol [11,13,18,21,20 ] methanol, aqueous glucoside )

Ground root bark of S. kunthianum was extracted of cyclohexane–ethylacetate and me thanol. with petrol ether–ethylacetate 1:1 each at room Eluents of 30% ethylacetate in cyclohexane on temperature. The solvent was evaporated under further fractionation using reversed -phase HPLC reduced pressure at 40°C and the residue (methanol–H2O 45:55 to 80:20) gave various subjected to column chromatography over silica weights of fractions whose structures (Fig . 4) gel. It was eluted with increasingly polar mixtures were elucidated by comprehensive analysis of

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their 1D and 2D NMR data as compound 13 Carrageenan-induced oedema is a model of (sterekunthal B), 14 (pyranokunthone A) and 15 acute inflammation in the study of non-steroidal (pyranokunthone B) . Further purification yielded anti-inflammatory drugs and suitable for compound 11 (pinnatal), 12 (sterekunthal A) and evaluating the anti-oedematous effects of natural 16 (anthrakunthone) [10]. products [24,25]. The model is believed to be biphasic; phase one involves the release of 3. PHARMACOLOGICAL PROFILE OF inflammatory mediators such as serotonin and S. kunthianum histamine while phase two is associated with prostaglandin release mediated by kinin. The Scientific investigation of ethnomedicinal claims anti-inflammatory activity of S. kunthianum is of S. kunthianum have been carried out probably due to the inhibition of prostaglandin pharmacologically. Some of the pharmacologic synthesis and cyclooxygenase products [23,22]. parameters investigated using crude extracts or This makes S. kunthianum a target for search for isolated compounds were antibacterial, anti- potential anti-inflammatory drug to add to existing inflammatory, analgesic, antiplasmodial, ones. antdiarrhoeal, antconvulsant and antioxidant activities, Table 2. The in vivo anti-inflammatory activities of β- sitosterol and β-sitosterol glucoside which are 3.1 Antibacterial Activity phytosterols of S. kunthianum have been reported [20]. [26] (2006) reported the in vivo Antibacterial activity of S. kunthianum was effect of β-sitosterol in a model of delayed-type evaluated using ethanol, ethyl-acetate and hypersensitivity in which they reveal the cell- petroleum ether of leaves and stem bark extracts mediated modulation of oedema via a by well diffusion method against Staphylococcus. mechanism other than the arachidonic acid and aureus, E. coli, typhi, Klebsiela spp , leukocyte inhibitory pathways. and [11,15]. Results emerging from the study show that lipophilic leaf 3.3 Analgesic Activity extracts of S. kunthianum exhibited significant antibacterial activity against tested organisms Thermal stimulus (hot plate test), mechanical [11]. The zones of inhibition of bacterial growth of stimulus (tail flick test) and chemically induced the extract at 30 mg/ml were Staphylococcus tissue damage (acetic acid-induced writhing and aureus 35 mm, E. coli 23 mm, Salmonella typhi formalin pain test) in mice/rats were employed to 25 mm, Klebsiela spp 28 mm and Aeromonas evaluate analgesic activity of aqueous extract of hydrophila 28 mm. However, Pseudomonas S. kunthianum . The aqueous extract (100, 200 or aeruginosa was resistant to the extract. The 400 mg/kg b. wt.) produced a significant dose- mechanism by which S. kunthianum exert dependent increase in pain threshold, increased antibacterial activity is unknown. More definitive tail flick latency in rats, inhibition of abdominal comparative study and resistance profile is writhes in mice and inhibited both phases of required to ascertain the efficacy of the extracts formalin pain test in mice with more effect on the and isolated compounds of S. kunthianum as first phase [8,22]. The analgesic effect of S. antibacterial agent before introduction to clinical kunthianum is typical of central and peripheral setting. analgesic acting agents. Perhaps, this suggests that aqueous extract of S. kunthianum acts via 3.2 Anti-inflammatory Activity similar mechanism and may find use as analgesic agent. The anti-inflammatory activity of aqueous extract of stem bark of S. kunthianum was investigated 3.4 Antiplasmodial Activity by [23] in rats using Carrageenan-induced paw oedema, leucocytes migration and granuloma air Evaluation of the antiplasmodial activity of pouch test at 3 h post-treatment showed petroleum ether fraction of root extract of S. pronounced effect of the extract at a dose of 400 kunthianum in vitro against two strains of P. mg/kg b. wt. and comparable to indomethacin at falciparum carried out by [10] using the method 10 mg/kg b. wt. Treatment with extract (400 described by [27], (1979). Isolated quinones from mg/kg b. wt.) or indomethacin (10 mg/kg b. wt.) S. kunthianum showed different degrees of prior to Carrageenan induced paw oedema antiplasmodial activity against chloroquine reduced peritoneal exudates volume by 24.93% resistant strain of P. falciparum and chloroquine and 26.88% of control respectively [ 23]. sensitive strain of P. falciparum with sterekunthal

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A being the most active against both strains [10]. 400 mg/kg b. wt. demonstrated anticonvulsant Mean IC50 values obtained for the fractions were activity in rodents [29]. This result validates the 5.6±0.6 µg/ml and 3.6±0.96 µg/ml pinnatal use of the aqueous stem bark extract by 1.3±0.1 µg/ml and 0.4±0.1 µg/ml sterekunthal A, traditional medicine dealers for the treatment of 23.3±4.2 µg/ml and 15.2±1.7 µg/ml sterekunthal childhood convulsions. B, 14.7±0.25 µg/ml and 14.7±05.3 µg/ml anthrakumthone, 11.7±4.0 µg/ml and > 25.0 3.7 Antioxidant Activity µg/ml pyranokunthal A, 8.9±1.2 µg/ml and 7.8±1.3 µg/ml pyranokunthone B against Phytocompounds like flavonoids and phenolic chloroquine resistant and chloroquine sensitive acid commonly found in plants have been shown P. falciparum respectively [10]. The result is to possess antioxidant activities and multiple indicative of a probable “lead” to a novel and biological effects by different mechanisms potent antimalarial thus making available to [30,31,21,19]. Antioxidants with free radical clinicians an additional “armour” to combat scavenging activities of extracts of S. kunthianum malaria a disease with high mortality rate among may have great relevance in the prevention and under five and pregnant women in the tropics. therapeutics of several diseases in which free radicals are implicated. The antioxidant activity of 3.5 Antidiarrhoeal/Antispasmolytic three (aqueous, methanol and aqueous-acetone) Activity extracts of S. kunthianum was evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH), ferric The antidiarrhoeal effect of 3,7,4̍-trihydroxy-3-(8̍ ̍̍- reducing/antioxidant powder (FRAP) and 2,2̍- acetoxy-7̍̍-methyloctyl)-5,6-dimethoxyflavone a azinobis(3-ethylbenzoline-6-sulphonate (ABTS) flavonoid isolated from the stem bark aqueous methods. extract of S. kunthianum was investigated using rodent models of castor oil-induced Results from the study carried out by [18] (2011) gastrointestinal motility and castor oil-induced showed that the aqueous acetone extract had diarrhoea. The result indicate that pre-treatment the best antioxidant and xanthine oxidase with dimethoxyflavone (25 mg/kg b. wt. or 50 inhibitory activities. The antioxidant and xanthine mg/kg b. wt.) caused a delay in the onset of oxidase inhibitory activities may be due to the diarrhoea, reduction in the frequency and weight mixture of flavonoids and polyphenols present in of wet stools compared to distilled water used as the aqueous acetone extract as quantified using negative control [12]. high-performance liquid chromatography-mass spectrometry (HPLC-MS) [18,21]. The antispasmolytic effect at doses of 25 mg/kg b. wt. or 50 mg/kg b. wt. was higher than 10 4. TOXICITY PROFILE OF mg/kg b. wt. of morphine but with no effect on Stereospermum kunthianum castor oil-induced intestinal fluid accumulation in rats and on normal gastrointestinal transit in mice Acute and sub-acute toxicity studies of the [12]. Although flavonoids are known for their aqueous extract of S. kunthianum stem bark ability to inhibit intestinal motility and hydro- show that the aqueous extract has a wide safety electrolytic secretions induced by prostaglandins margin as no adverse effect was observed in E2 [28,12], the result from this study suggest that experimental animals when used at doses up to the antidiarrhoeal activity of S. kunthianum is due 1000 mg/kg b. wt. as reported by [33]. Marginal to antispasmolytic effect rather than inhibition of enlargement of organs such as liver, kidney, hydro-electrolytic secretion [12]. Investigation of heart and spleen with no histological changes the cellular mechanism by which was observed in rats treated with aqueous dimethoxyflavone exerts antispasmolytic activity extract of S. kunthianum . Parameters such as is necessary to know if it will be most suitable liver enzymes and serum biochemical compared to clinically used antispasmolytic components evaluated; alanine aminotransferase agents with pronounced undesirable (ALT), alkaline phosphatase (AST), total antimuscarinic side effects. cholesterol, low density lipoprotein (LDL), high density lipoprotein (HDL) and triglycerides 3.6 Anticonvulsant Activity showed no significant deviation from the normal range [33]. S. kunthianum extract could therefore The anticonvulsant activity of S. kunthianum was be used for long term treatment or management reported by [29]. In the study aqueous extract of of acute or chronic conditions which it is stem bark of S. kunthianum at the dose of 100 to pharmacologically indicated .

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11 (R=OH) 12 13 (R=H)

14 15 16

Fig. 4. Chemical structures of quinones of S. kunthianum

Table 2. Pharmacological profile of Stereospermum kunthianum

Plant part Type of extract Pharmacologic activity Reference Leave Petroleum ether extract, Antibacterial [11,22,32,15] methanol extract, hexane extract Stem bark Aqueous extract Anti-inflammatory [29,22,20] Petroleum ether extract Stem bark Aqueous extract Analgesic [8,22] Leave Petroleum ether extract Antiplasmodial [10,22] Stem bark Aqueous extract Antidiarrhoael [12,22] Stem bark Aqueous extract Anticonvulsant [29] Aqueous acetone extract Antioxidant [18,19,20] Petroleum ether extract

The cytoxicity proliferation assay of the isolated savannah regions of Africa and Asia. This review quinones from petroleum ether root extract is an appraisal of the phytochemical, showed that pinnatal, sterekunthal A, pharmacological and toxicological profile of the sterekunthal B, anthrakunthone exhibited marked plant species which revealed the presence of non selective cytotoxicity against human tannins, saponins, glycosides, sterols and endothelial (ECV-304) cell [34]. Mean IC 50 values various phenolic compounds . Isolation and obtained was 2.2±0.3 µg/ml pinnatal, 0.9±0.02 characterization of chemical compounds from the µg/ml sterekunthal A, 16±1.0 µg/ml sterekunthal various part of the plant revealed that iridoid B, 7.9±0.5 µg/ml anthrakunthone, while glycosides, flavonoids and quinones are pyranokunthone A >200.0 µg/ml and predominant phytochemicals present in the plant. pyranokunthone B 88.2±4.6 µg/ml display much Isolated compounds of coumarins and sterols are less cytotoxicity and more selective against not uncommon. Extracts and pure compounds P. falciparum [34]. from S. kunthianum have been shown to exhibit numerous pharmacological activities. The 5. CONCLUSION therapeutic potentials of various fractions and isolated compounds of S. kunthianum as S. kunthianum is a medicinal plant widely validated in the studies so reviewed provides a distributed and used in the Sudano-Guinea platform for further investigation on the

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albricans . J Applied Pharm. Sci. 2012; Sandrine Petit) stem bark. J Pharmacy 02(01):45-50. Bioresources. 2013;10(2). 34. Okpo SO, Ching FP. Sub-acute toxicity Available:http://dx.doi.org/10.43114/jpb.v1 studies on the aqueous extracts of 0i2.1 (Accessed on 0/8/2015) Stereospermum kunthianum (Cham, ______© 2016 Oloche et al.; This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0 ), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Peer-review history: The peer review history for this paper can be accessed here: http://sciencedomain.org/review-history/11698

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